Mac's toerail bolts
Mac, your best bet is, when you can, to remove those 'chainplates' (angled bit of SS plate) and to inspect the toerail under it. Most likely it has become corroded. The proper fix then is to etch the metal and fill with some kind of epoxy, such as WEST-system's with aluminum shavings, and then seal with UV barrier such as varnish or paint. In some places on mine I merely scratched it clean and 'filled' with black 4200. Though it showed some signs of corrosion, it was in remarkably good shape for an example of stainless steel bolted directly to aluminum, with no insulator, after 40 years.
Any time I have to remove a toerail bolt for anything, it goes back as a new SS 1/4-20 HHCS (hex head cap screw) with a Delrin washer under the head and a wider SS fender washer under the flange, with 4200 or 5200 to seal the threads in the hole and under the head. (I use HHCS for everything going through the deck or hull because it makes the next removal a one-man job, with the help of a vise-grip or box-end wrench left alone on one side.) For some reason the factory used bronze washers for these, thus imposing tri-metallic corrosion: aluminum rail + SS carriage bolts + bronze washers = worst possible combination. By now the bronze washers under the flange are pretty blue; but they are not pink yet. And they lasted 40 years on my boat and the rail still does not leak.
When I am done painting the hull and deck this season, I will run a bead of black 4200 Fast-Cure along the inside and outside. The bead along the deck and rail will be done first, to allow anything under the rail to get out. Later-- almost right before commissioning time-- I will run another bead along the hull and rail. This can be done very tidily by the use of decent fine-line tape, allowing maybe 3/16" for the bead itself. Then run a finger, wet with tap water, along the bead to skin it over before removing the tape, and allow a full 3-4 days for it to cure before walking or washing near it.
All my stanchion bases and their braces are bolted through the toerail. Also, I replaced the bent-SS plate with 2500-lb SS U-bolts for the shroud attachments. I have two more at the after corners for the backstay and will be adding two more for running backstays as well. All of this hardware, properly bedded and sized, will add strength and stiffness to the toerail, which is by design and by default the strongest element of the whole boat.
From the factory the toerail was bedded in 5200. I would not, for any reason, use anything less than 4200 for this, and then only if it's all I happen to have. It is NOT an application in which butyl tape is appropriate; as butyl tape has very minimal strength in either shear or tensile loads, both of which affect the toerail. The same goes for silicone, for the same reasons. Even just a properly-applied bead along the edges, done in 4200/5200, will add stiffness and keep out all water.
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